On Dec. 28, 2011, Boston Red Sox general manager Ben Cherington decided New Year’s Eve was too long to wait for fireworks.
Reaching out to the Oakland A’s, Cherington made a big finish move, acquiring future pitching coach and two-time All-Star closer Andrew Bailey and outfielder Ryan Sweeney from Oakland. At the time, the move was praised, with ESPN’s David Schoenfield calling it a “smart” trade for the Sox, even though he felt the trade left some questions unanswered.
Oakland received outfielder Josh Reddick, right-handed pitcher Raúl Alcántara, and career minor leaguer Miles Head.
Bailey was an all-star in 2009 and 2010 and was the American League Rookie of the Year in 2009. In his three years with the A’s, he posted a 7-10 record with a 2.07 ERA and 75 saves. Bailey’s career as the closer for the Sox was injury-plagued, and after two years, the Red Sox moved on after he posted a 4-2 record with a 4.91 ERA and 14 saves in 44.0 IP.
The Red Sox acquired reliever turned pitching coach Andrew Bailey from the Athletics on Dec. 28, 2011
While Bailey’s tenure as a pitcher didn’t work out the way Cherington planned, it did help pave the way for his eventual return to the Red Sox as the pitching coach. Bailey played with Red Sox chief baseball officer Craig Breslow in Oakland and Boston. In 2023, Bailey was looking for a change of scenery after serving as the San Fransisco Giants pitching coach from 2020-2023. Over that time, the Giants ranked sixth in the majors in ERA (3.80) while posting the third-best strikeout-to-walk ratio and a league-low 525 home runs.
From go, Bailey has seemed like the perfect guy for the job. Speaking to Sirius XM’s MLB Network, he talked about being a part of a Red Sox team that went from struggling in 2012 to a World Series Champion in 2013.
"We were a last-place team in 2012 and then won the World Series in 2013, so we kind of ran the gamut of experiences. [Boston is] such a special place. The fan base is amazing. And ultimately, it’s one of the greatest to win in. Their fans are electric, and the environment there."Boston pitching Coach Andrew Bailey
Taking his attitude to the field, Bailey and the Red Sox pitching staff saw an instant improvement in 2024. The Sox cut their fastball usage, something Bailey had preached in San Fransisco, and According to Schoenfield, the starting rotation posted the best ERA across the first 35 games of the season since the 1981 Dodgers.
Injuries hampered the Red Sox for most of the 2024 season, but overall, the team's pitching did improve. Headed into 2025, the Red Sox have made key additions, adding several relief arms to minor league deals and some big names to the starting rotation, including Chicago White Sox all-star Garrett Crochet and two-time World Series Champion Walker Buehler.
In the short term, the trade for Bailey didn’t pan out the way the Red Sox hoped, but looking ahead to 2025, there is still potential for fireworks from this December 28th deal.